CN113056452B - Compound and organic light-emitting diode comprising same - Google Patents
Compound and organic light-emitting diode comprising same Download PDFInfo
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- CN113056452B CN113056452B CN201980075891.8A CN201980075891A CN113056452B CN 113056452 B CN113056452 B CN 113056452B CN 201980075891 A CN201980075891 A CN 201980075891A CN 113056452 B CN113056452 B CN 113056452B
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- IURRXCRWRKQLGC-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 IURRXCRWRKQLGC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present application claims priority from korean patent application No. 10-2018-0164377, filed to the korean patent office on 12 months 18 of 2018, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode, electrons are injected into the organic layer from the cathode, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
R 1 to R 9 Are each, independently of one another, hydrogen, deuterium, nitrile, halogen radicals, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
R 1 、R 2 、R 4 、R 5 、R 7 and R is 8 Any one of which is connected with L 3 In combination with the fact that,
L 1 and L 2 Are identical or different from one another and are each independently of one another a substituted or unsubstituted arylene group,
L 3 in order to bond directly to each other,
Ar 1 and Ar is a group 2 Are identical or different from each other and are each independently substituted or unsubstitutedSubstituted aryl, or substituted or unsubstituted heteroaryl,
m and n are the same or different from each other and each independently is an integer of 0 to 2,
when m is 2, the above L 1 The same as or different from each other,
when n is 2, the above L 2 The same as or different from each other.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more layers of the organic layer contain the compound.
Effects of the invention
The compound according to an embodiment of the present specification may be used as a material of an organic layer of an organic light emitting device, and by using the compound, an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics can be achieved in the organic light emitting device.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to an embodiment of the present specification.
[ description of the symbols ]
1: substrate board
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electron suppression layer
8: light-emitting layer
9: hole blocking layer
10: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the above chemical formula 1.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or more substituents selected from deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or substituted with 2 or more substituents selected from the above exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be aryl substituted with aryl, aryl substituted with heteroaryl, heterocyclic group substituted with aryl, aryl substituted with alkyl, or the like.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, more preferably a cycloalkyl group having 3 to 20 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
In the present specification, the amine group may be selected from the group consisting of-NH 2 The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methylanthracenylamine group, a diphenylamino group, an N-phenylnaphthylamino group, a xylylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.
In the present specification, the silyl group may be represented by the chemical formula-SiRaRbRc, and the above Ra, rb, and Rc may be the same as or different from each other, and each may be independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 20. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms, more specifically 10 to 20 carbon atoms. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, an "adjacent" group refers to a substituent substituted on an atom directly bonded to an atom substituted with the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamino group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The above arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group.
In this specification, a heteroaryl group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, more preferably 2 to 20, and the heteroaryl group may be a single ring or a multiple ring. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In one embodiment of the present specification, the chemical formula 1 is a compound represented by any one of the following chemical formulas 1-1 to 1-3.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3,
L 1 、L 2 、L 3 、R 1 to R 9 、Ar 1 、Ar 2 M and n are as defined in chemical formula 1 above.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted or unsubstituted arylene groups having 6 to 20 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical or different from one another and are each independently substituted arylene groups having 6 to 20 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Are identical to or different from each other and are each independently an unsubstituted arylene group having 6 to 20 carbon atoms.
In one embodiment of the present specification, the L 1 And L 2 Each of which is the same or different from the other, is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group having a valence of 2, a substituted or unsubstituted terphenyl group having a valence of 2, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group having a valence of 2, a substituted or unsubstituted phenanthryl group having a valence of 2, a substituted or unsubstituted triphenylenyl group having a valence of 2, or a substituted or unsubstituted fluorenyl group having a valence of 2.
In one embodiment of the present specification, the L 1 And L 2 Are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group having a valence of 2.
In one embodiment of the present specification, the L 1 And L 2 Are the same or different from each other and are each independently phenylene, naphthyl or biphenyl having a valence of 2.
In one embodiment of the present specification, the L 1 And L 2 Is phenylene.
In one embodiment of the present specification, the L 1 And L 2 Is naphthyl.
In one embodiment of the present specification, the L 1 And L 2 Biphenyl is 2-valent.
In one embodiment of the present specification, the L 1 And L 2 Each independently is phenylene, naphthyl, or 2-valent biphenyl.
In one embodiment of the present specification, the L 3 Is a direct bond.
In one embodiment of the present specification, m is 0.
In one embodiment of the present specification, m is 1.
In one embodiment of the present specification, m is 2.
In one embodiment of the present specification, n is 0.
In one embodiment of the present specification, n is 1.
In one embodiment of the present specification, n is 2.
In one embodiment of the present specification, when m and n are 0, they are directly bonded.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Identical to each other, is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Identical to each other, isSubstituted aryl groups having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Identical to each other, is an unsubstituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Identical to each other, are substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Identical to each other, are substituted heteroaryl groups having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Identical to each other, are unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Different from each other.
In one embodiment of the present specification, ar is as described above 1 Is a substituted aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 Is an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 Is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 Is a substituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 Is an unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 2 Is an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, ar is as described above 2 Is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 2 Is a substituted heteroaryl group having 3 to 30 carbon atoms.
In an embodiment of the present specificationIn an embodiment, ar is as described above 2 Is an unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are the same as or different from each other, and each is independently any one of the substituents described below.
The dotted line is L 1 And L 2 The binding site, rx, refers to alkyl and aryl.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, dibenzofuranyl or dibenzothiophenyl,
the above-mentioned phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylene group, fluorenyl group, dibenzofuranyl group or dibenzothiophenyl group is substituted or unsubstituted with any one or more substituents selected from deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group.
In one embodiment of the present specification, ar is as described above 1 And Ar is a group 2 Are identical to or different from one another and are each, independently of one another, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, dibenzofuranyl or dibenzothiophenyl,
the above-mentioned phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, triphenylene group, fluorenyl group, dibenzofuranyl group or dibenzothiophenyl group is substituted or unsubstituted with any one or more substituents selected from deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
In one embodiment of the present specification, R is 1 To R 9 Is not in accordance with the L 3 The combined substituents being hydrogenDeuterium, nitrile, halogen, nitro, substituted or unsubstituted alkyl of 1 to 10 carbon atoms, substituted or unsubstituted alkoxy of 1 to 10 carbon atoms, silyl substituted with alkyl of 1 to 10 carbon atoms, substituted or unsubstituted alkenyl of 1 to 10 carbon atoms, substituted or unsubstituted aryl of 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms.
In one embodiment of the present specification, R is 1 To R 8 Is not in accordance with the L 3 The combined substituent is hydrogen; deuterium; a nitrile group; f, performing the process; br; cl; i, a step of I; a nitro group; a methyl group; an ethyl group; a propyl group; an isopropyl group; a butyl group; a tertiary butyl group; methoxy; an ethoxy group; butoxy; t-butoxy; silyl substituted with methyl, ethyl or tert-butyl; a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; phenanthryl; an anthracene group; dibenzofuranyl; dibenzothienyl; carbazolyl or triazinyl.
In one embodiment of the present specification, R is 1 To R 8 Is not in accordance with the L 3 The substituents attached are hydrogen.
In one embodiment of the present specification, R is 9 Is hydrogen, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 30 carbon atoms.
In one embodiment of the present specification, R is 9 Is an aryl group having 6 to 20 carbon atoms.
In one embodiment of the present specification, R is 9 Is phenyl, biphenyl or terphenyl.
In one embodiment of the present specification, R is 9 Is phenyl.
In one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
The organic light emitting device of the present invention includes: the organic light-emitting device includes a first electrode, a second electrode provided opposite to the first electrode, and 1 or 2 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers may contain the compound.
For example, the structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
The above-described fig. 1 illustrates an organic light emitting device, and is not limited thereto.
Fig. 2 illustrates a structure of an organic light emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked on a substrate 1. The compound of the present invention can be used for the above-mentioned hole injection layer, hole transport layer, electron suppression layer, light-emitting layer, hole blocking layer, electron injection and transport layer, but is preferably used for the electron suppression layer.
The above-described fig. 2 illustrates an organic light emitting device, and is not limited thereto.
In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of formula 1.
In an embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the compound of chemical formula 1.
In an embodiment of the present invention, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer may include the compound of formula 1.
In an embodiment of the present invention, the organic layer includes an electron inhibiting layer, and the electron inhibiting layer may include the compound of formula 1.
In an embodiment of the present invention, the organic layer includes a hole blocking layer, and the hole blocking layer may include the compound of formula 1.
In an embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the compound of formula 1.
For example, the organic light emitting device according to the present invention may be manufactured as follows: PVD (physical vapor deposition) method such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) is used to vapor deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic layer including a compound of the above chemical formula 1 are formed on the anode, and then a substance that can be used as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDT), polypyrrole and polyaniline, etc., but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection material is a material that can well inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer.
The hole-transporting substance is preferably a substance which can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and has a large mobility to the holes. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxy-quinoline aluminum complex (Alq 3 ) Carbazole-based compound, dimeric styryl (dimeric styryl) compound, BAlq, 10-hydroxybenzoquinoline metal compound, benzoThe azole, benzothiazole, benzimidazole compound, poly (p-phenylene vinylene) (PPV) polymer, spiro (spiro) compound, polyfluorene, rubrene, and the like, but are not limited thereto.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that 1 or more of the organic layers are formed using the above-described compounds.
The present specification also provides a method of manufacturing an organic light emitting device formed using the above compound.
Examples of the dopant material include aromatic compounds, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic compound is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,And bisindenopyrene, etc., wherein the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium, samarium, etc., and in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenones are presentAnthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that blocks holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazolyl derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The method of manufacturing the compound of chemical formula 1 above and the manufacture of an organic light emitting device using the same are specifically described in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
In the following reaction formulae, the kinds and numbers of substituents can be appropriately selected by those skilled in the art to synthesize various types of intermediates by appropriately selecting known starting materials. The kind of reaction and the reaction conditions may be employed by techniques known in the art.
If the production formula described in the examples of the present specification and the above intermediate are appropriately combined based on common technical knowledge, all the compounds of the above chemical formula 1 described in the present specification can be produced.
Production example 1
After complete dissolution of compound a-1 (13.96 g,24.84 mmol) and compound a1 (7.50 g,24.35 mmol) in 280mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.51 g,36.53 mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.12 g,0.24 mmol) was added, and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give Compound 1 (12.17 g, yield: 63%).
MS[M+H] + ＝791
Production example 2
After compound B-1 (16.79 g,29.88 mmol) and compound a2 (7.50 g,29.30 mmol) were completely dissolved in 290mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (4.22 g,43.95 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.15 g,0.29 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give Compound 2 (11.97 g, yield: 55%).
MS[M+H] + ＝739
Production example 3
After compound C-1 (12.95 g,23.04 mmol) and compound a3 (7.50 g,22.59 mmol) were completely dissolved in 270mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.26 g,33.89 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.12 g,0.23 mmol) was added, and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of ethyl acetate to give Compound 3 (13.86 g, yield: 75%).
MS[M+H] + ＝815
Production example 4
After complete dissolution of compound a-2 (22.73 g,37.14 mmol) and compound a4 (7.50 g,36.41 mmol) in 280mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (5.25 g,54.61 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.19 g,0.36 mmol) was added and heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate to give Compound 4 (11.39 g, yield: 42%).
MS[M+H] + ＝739
Production example 5
After compound B-2 (22.73 g,37.14 mmol) and compound a5 (7.50 g,36.41 mmol) were completely dissolved in 290mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (5.25 g,54.61 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.19 g,0.36 mmol) was added, and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give Compound 5 (9.65 g, yield: 36%).
MS[M+H] + ＝739
Production example 6
After compound C-2 (15.20 g,24.84 mmol), and compound a6 (7.50 g,24.35 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.51 g,36.53 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.12 g,0.24 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 6 (10.05 g, yield: 56%).
MS[M+H] + ＝738
PREPARATION EXAMPLE 7
After complete dissolution of compound a-3 (15.30 g,25.00 mmol) and compound a7 (7.50 g,24.51 mmol) in 260mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (3.53 g,36.76 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.13 g,0.25 mmol) was added followed by stirring with heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 210mL of ethyl acetate to give Compound 7 (14.46 g, yield: 70%).
MS[M+H] + ＝839
Production example 8
After compound B-3 (16.60 g,27.13 mmol) and compound a8 (7.50 g,26.60 mmol) were completely dissolved in 280mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.83 g,39.89 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.27 mmol) was added, and the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give Compound 8 (16.27 g, yield: 73%).
MS[M+H] + ＝815
Production example 9
After compound C-3 (16.60 g,27.13 mmol), and compound a9 (7.50 g,26.60 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.83 g,39.89 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.14 g,0.27 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 220mL of tetrahydrofuran, whereby Compound 9 (13.27 g, yield: 61%) was produced.
MS[M+H] + ＝815
Production example 10
After complete dissolution of compound a-4 (18.72 g,31.10 mmol) and compound a10 (7.50 g,30.49 mmol) in 290mL of xylene under nitrogen atmosphere in a 500mL round bottom flask, naOtBu (4.39 g,45.73 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.16 g,0.30 mmol) was added and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 260mL of ethyl acetate to give compound 10 (9.78 g, yield: 42%).
MS[M+H] + ＝769
Production example 11
After compound B-4 (17.58 g,29.20 mmol), and compound a11 (7.50 g,28.63 mmol) were completely dissolved in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.13 g,42.94 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.15 g,0.29 mmol) was added, and then heated and stirred for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give compound 11 (10.05 g, yield: 45%).
MS[M+H] + ＝785
Production example 12
After compound C-4 (10.47 g,19.21 mmol), and compound a12 (4.50 g,16.54 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (3.18 g,33.09 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.08 g,0.17 mmol) was added, and then heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give compound 12 (8.76 g, yield: 76%).
MS[M+H] + ＝795
PREPARATION EXAMPLE 13
After compound C-1 (16.41 g,29.20 mmol), and compound a13 (7.50 g,28.63 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.13 g,42.94 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.15 g,0.29 mmol) was added, and then heated and stirred for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate to give compound 13 (8.46 g, yield: 40%).
MS[M+H] + ＝745
PREPARATION EXAMPLE 14
After compound B-1 (17.48 g,31.10 mmol) and compound a14 (7.50 g,30.49 mmol) were completely dissolved in 230mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.39 g,45.73 mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.16 g,0.30 mmol) was added, and then heated and stirred for 6 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give compound 14 (11.73 g, yield: 53%).
MS[M+H] + ＝729
Production example 15
After complete dissolution of compound a-1 (18.53 g,32.97 mmol) and compound a15 (7.50 g,32.33 mmol) in 240mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (4.66 g,48.49 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.17 g,0.32 mmol) was added and heated and stirred for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate to give compound 15 (9.76 g, yield: 42%).
MS[M+H] + ＝715
Example 1-1
To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 is added>Vacuum evaporation is performed to form a hole transport layer. Next, compound 1 is coated with a film thickness +.>Vacuum vapor deposition is performed to form an electron suppression layer. Next, on the above electron suppression layer, the film thickness is +.>A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. On the above light-emitting layer, a compound represented by the following chemical formula HB1 is represented by a film thickness +.>Vacuum evaporation is performed to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form ∈ ->Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And vapor deposition is performed to the thickness of the substrate, thereby forming a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device.
Examples 1-2 to 1-24
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of compound 1.
Comparative examples 1-1 to 1-4
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of compound 1. Compounds of EB2, EB3, EB4 and EB5 used in table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting device using the compound of the present invention as an electron suppression layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device. In examples 1-1 to 1-15, it was found that when a substance in which an amino-branched biphenyl (phenylene group substituted with phenyl) -polycyclic heteroaryl group was sequentially bonded was used as an electron-inhibiting layer, the branched biphenyl group acted to push electrons further toward the amino group, and thus exhibited characteristics of low voltage, high efficiency, and long life.
In comparative examples 1 and 2, when an amine group was bonded in the para-position (No. 3, no. 6) of N of carbazole and the No. 9 direction of carbazole, the properties were inferior to those of the compound of the present invention in terms of efficiency, driving voltage and stability.
While the preferred embodiment (electron suppression layer) of the present invention has been described above, the present invention is not limited thereto, and it is also within the scope of the present invention that the present invention can be modified and implemented in various forms within the scope of the claims and the detailed description of the invention.
Claims (10)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein in the chemical formula 1 described above, a compound having the formula,
R 1 to R 8 Are identical or different from each other and are each independently hydrogen or deuterium,
R 9 is an aryl group having 6 to 20 carbon atoms,
R 1 、R 2 、R 4 、R 5 、R 7 and R is 8 Any one of which is connected with L 3 In combination with the fact that,
L 1 and L 2 Are identical or different from one another and are each independently of one another arylene radicals having 6 to 20 carbon atoms,
L 3 in order to bond directly to each other,
Ar 1 and Ar is a group 2 Are the same or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, an alkyl group having 1 to 10 carbon atoms, or a silyl group represented by the formula of-sirrbrc; dibenzofuranyl or dibenzothienyl, wherein Ra, rb and Rc are the same or different from each other and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,
m and n are the same or different from each other and are each independently an integer of 0 to 2,
when m is 2, the L 1 Identical or different from each other
When n is 2, the L 2 The same as or different from each other.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Wherein in the chemical formulas 1-1 to 1-3, L 1 、L 2 、L 3 、R 9 、Ar 1 、Ar 2 M and n are as defined in the chemical formula 1,
R 1 to R 8 Each independently is hydrogen.
3. The compound of claim 1, wherein L 1 And L 2 Are identical or different from one another and are each independently phenylene, naphthylene or biphenyl having a valence of 2.
4. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Are identical to or different from each other and are each independently an aryl group having 6 to 20 carbon atoms, a dibenzofuranyl group or a dibenzothienyl group.
5. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
6. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode in 1 or 2 layers or more, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 5.
7. The organic light-emitting device of claim 6, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound.
8. The organic light-emitting device of claim 6, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.
9. The organic light-emitting device of claim 6, wherein the organic layer comprises an electron-inhibiting layer, wherein the electron-inhibiting layer comprises the compound.
10. The organic light-emitting device of claim 6, wherein the organic layer comprises a light-emitting layer comprising the compound.
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| KR20160004513A (en) * | 2014-07-03 | 2016-01-13 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN107652223A (en) * | 2017-10-10 | 2018-02-02 | 上海道亦化工科技有限公司 | A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device |
| KR20180082124A (en) * | 2017-01-10 | 2018-07-18 | 에스에프씨 주식회사 | organic light-emitting diode with High efficiency |
| KR20180096458A (en) * | 2017-02-21 | 2018-08-29 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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| KR20160004513A (en) * | 2014-07-03 | 2016-01-13 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20180082124A (en) * | 2017-01-10 | 2018-07-18 | 에스에프씨 주식회사 | organic light-emitting diode with High efficiency |
| KR20180096458A (en) * | 2017-02-21 | 2018-08-29 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| CN107652223A (en) * | 2017-10-10 | 2018-02-02 | 上海道亦化工科技有限公司 | A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device |
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